Atrazine
General
Systematic name	1-chloro-3-ethylamino-5-isopropylamino-2,4,6-triazine
Other names	atrazine see also synonyms
Molecular formula	C8H14ClN5
SMILES	ClC1=NC(NC(C)C) =NC(NCC)=N1
Molar mass	215.685 g/mol
Appearance	Solid, colorless crystal
CAS number	[1912-24-9]
Properties
Density and phase	1.187 g/cm³, ?
Solubility in water	.007 g/100 ml (?°C)
Melting point	175°C (? K)
Boiling point	200°C (? K)
Acidity (pKa)	?
Basicity (pKb)	?
Chiral rotation [α]D	?°
Viscosity	? cP at ?°C
Structure
Molecular shape	?
Coordination geometry	?
Crystal structure	?
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704
Flash point	?°C
R/S statement	R: ? S: ?
RTECS number	?
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Other anions	?
Other cations	?
Related ?	?
Related compounds	?
Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references

Atrazine, 2-chloro-4-(ethylamine)-6-(isopropylamine)-s-triazine, is an s-triazine-ring herbicide that is used globally to stop pre- and post-emergence broadleaf and grassy weeds in major crops. Atrazine binds to the plastoquinone-binding protein in photosystem II, inhibiting electron transport. Atrazine is one of the most widely used herbicides and according to the Environmental Protection Agency (EPA) the U.S. used 77 million lb of Atrazine in 2003. Image File history File links Atrazine. ... Image File history File links Size of this preview: 800 × 558 pixelsFull resolution (1100 × 767 pixel, file size: 185 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... Atrazine, 2-chloro-4-(ethylamine)-6-(isopropylamine)-s-triazine, is an s-triazine-ring herbicide that is used globally to stop pre- and post-emergence broadleaf and grassy weeds in major crops. ... This article or section does not cite any references or sources. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... This article does not cite any references or sources. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... 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The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate... The specific rotation of a chemical compound [α] is defined as the observed angle of optical rotation α when plane-polarized light is passed through a sample with a path length of 1 decimeter and a sample concentration of 1 gram per 1 millilitre. ... Viscosity is a measure of the resistance of a fluid to deform under shear stress. ... 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In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... A triazine is one of three organic chemicals, isomeric with each other, whose empirical formula is C3H3N3. ... A herbicide is a pesticide used to kill unwanted plants. ... Yellow starthistle, a thistle native to southern Europe and the Middle East that is an invasive weed in parts of North America. ... Plastoquinone Plastoquinone, often abbreviated pq, is a molecule used in the electron transport chain in the light-dependent reactions of photosynthesis. ... A representation of the 3D structure of myoglobin, showing coloured alpha helices. ... In the process of photosynthesis, light is absorbed by a photosystem (ancient Greek: phos = light and systema = assembly) to begin an energy-producing reaction. ... The electron transfer chain (also called the electron transport chain, or simply electron transport), is a series of protein complexers and lipid messengers spanning the inner mitochondrial membrane that accepts electrons from electron donors such as NADH or succinate, shuttles these electrons from within the mitochondrial matrix across the inner... EPA redirects here. ... The pound or pound-mass (abbreviations: lb, lbm, or sometimes in the United States, #) is a unit of mass (sometimes called weight in everyday parlance) in a number of different systems, including English units, Imperial units, and United States customary units. ...

The half-life of atrazine in soil is 15 to 100 days. Atrazine and its derivatives are used in many industrial processes as well, including use in dyes and explosives. Hydroxyatrazine is unregulated and no negative effect is known. However, atrazine is the most widely used herbicide in conservation tillage systems, which is a system designed to help prevent soil erosion and runoff by as much as 90 percent. Half-Life For a quantity subject to exponential decay, the half-life is the time required for the quantity to fall to half of its initial value. ... Loess field in Germany Surface-water-gley developed in glacial till, Northern Ireland Technically, soil forms the pedosphere: the interface between the lithosphere (rocky part of the planet) and the biosphere, atmosphere, and hydrosphere. ... Look up dye in Wiktionary, the free dictionary. ... This article is concerned solely with chemical explosives. ...

The oral LD50 for atrazine is 3090 mg/kg in rats, 1750 mg/kg in mice, 750 mg/kg in rabbits, and 1000 mg/kg in hamsters. The dermal LD50 in rabbits is 7500 mg/kg and greater than 3000 mg/kg in rats. The 1-hour inhalation LC50 is greater than 0.7 mg/L in rats. The 4-hour inhalation LC50 is 5.2 mg/L in rats. An LD50 test being administered In toxicology, the LD50 or colloquially semilethal dose of a particular substance is a measure of how much constitutes a lethal dose. ... Species 50 species; see text *Several subfamilies of Muroids include animals called rats. ... Feral mouse A mouse (plural mice) is a rodent that belongs to one of numerous species of small mammals. ... Genera Pentalagus Bunolagus Nesolagus Romerolagus Brachylagus Sylvilagus Oryctolagus Poelagus Rabbits are small mammals in the family Leporidae of the order Lagomorpha, found in several parts of the world. ...

Biodegradation

The start of atrazine biodegradation can occur by three known ways. Atrazine can be dechlorinated and then the other ring substituents are removed by amidohydrolases. These steps are performed by AtzA-C respectively, which are commonly produced by a single organism. The end product, cyanuric acid, is then used as a carbon and nitrogen source. The most characterized organism that performs this pathway is Pseudomonas sp. strain ADP. The other mechanism involves dealkylation of the amino groups. In this mechanism dechlorination can be performed in the second step to eventually yield cyanuric acid, or the end result is 2-chloro-4-hydroxy-6-amino-1,3,5-triazine, which currently has no known path to further degradation. This path can occur by a single Pseudomonas species or by a number of bacteria.^[1][2] Biodegradation is the process by which organic substances are broken down by living organisms. ... Chlorination is the process of adding the element chlorine to water as a method of water purification to make it fit for human consumption as drinking water. ... In biochemistry, a hydrolase is an enzyme that can break a chemical bond by hydrolysis. ... “Life on Earth” redirects here. ... Cyanuric acid or 1,3,5-triazine-2,4,6-triol is an organic chemical compound with the chemical formula C3H3N3O3. ... Type species Pseudomonas aeruginosa Species group P. aeruginosa P. alcaligenes P. anguilliseptica P. argentinensis P. borbori P. citronellolis P. flavescens P. mendocina P. nitroreducens P. oleovorans P. pseudoalcaligenes P. resinovorans P. straminea group P. aurantiaca P. aureofaciens P. chlororaphis P. fragi P. lundensis P. taetrolens group P. antarctica P. azotoformans... In chemistry, especially in organic chemistry and biochemistry, an amino group is an ammonia-like functional group. ...

Sorption of atrazine in soil determines the bioavailability to degradation, which is performed mostly by microbes. Low atrazine biodegradation rates are a product of low solubility and sorption to areas inaccessible by bacteria. The addition of surfactants increases the solubility, increasing catalysis. Before use the surfactant must be evaluated for its effect on the environment as well as its use as a preferential carbon and energy source must be evaluated. Atrazine itself is a poor energy source due to the highly oxidized carbons in the ring. It is catabolized as a carbon and nitrogen source in limiting environments although the optimum carbon and nitrogen availability is not known. It has been shown that inorganic nitrogen increases atrazine catabolism while organic nitrogen decreases it. Low concentrations of glucose can have the effect of decreasing bioavailability though formation of bound atrazine, while higher concentrations promote the catabolism of atrazine.^[3] Sorption refers to the total action of both absorption and adsorption. ... Loess field in Germany Surface-water-gley developed in glacial till, Northern Ireland Technically, soil forms the pedosphere: the interface between the lithosphere (rocky part of the planet) and the biosphere, atmosphere, and hydrosphere. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A microorganism or microbe is an organism that is so small that it is microscopic (invisible to the naked eye). ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... Surfactants are wetting agents that lower the surface tension of a liquid, allowing easier spreading, and lower the interfacial tension between two liquids. ... In chemistry and biology, catalysis is the acceleration (increase in rate) of a chemical reaction by means of a substance, called a catalyst, that is itself not consumed by the overall reaction. ... Anabolism is the aspect of metabolism that contributes to growth. ... Glucose (Glc), a monosaccharide (or simple sugar), is an important carbohydrate in biology. ...

The genes AtzA-C have been found to be highly conserved in atrazine degrading organisms worldwide. This could be due to the mass transfer of AtzA-C on a global scale. In Pseudomonas sp. ADP, the atz genes are located non-contiguously on a plasmid with mercury catabolism genes as well. This plasmid is conjugatable to Gram negative bacteria in the lab and could easily lead to the worldwide distribution with the amount of atrazine and mercury being produced. AtzA-C have also been found in a Gram positive bacterium, but chromosomally located.^[4] This is not surprising due to the presence of insertion elements flanking each gene and the detection of these genes on different plasmids. Their configurations on these different plasmids suggest the insertion elements are involved in the assembly of this specialized catabolic pathway.^[2] Two options exist for degradation of atrazine using microbes: bioaugmentation or biostimulation.^[2] For a non-technical introduction to the topic, see Introduction to Genetics. ... Figure 1: Illustration of a bacterium with plasmids enclosed showing chromosomal DNA and plasmids. ... General Name, Symbol, Number mercury, Hg, 80 Chemical series transition metals Group, Period, Block 12, 6, d Appearance silvery Standard atomic weight 200. ... Bacterial conjugation is the transfer of genetic material between bacteria through cell-to-cell contact. ... Gram-negative Pseudomonas aeruginosa bacteria (pink-red rods). ... Gram-positive Bacillus anthracis bacteria (purple rods) in cerebrospinal fluid sample. ... Bioaugmentation refers to the introduction of a group of natural microbial strain or a genetically engineered variant so as to achive bioremediation. ... Biostimulation involves the modification of the environment to stimulate existing bacteria capable of bioremediation. ...

Controversy

Atrazine use in pounds per square mile by county. Atrazine is one of the most commonly used pesticides in the United States.^[5]

Atrazine has been banned in several European countries.^[6][7] However, the European Union scientific review stated, “It is expected that the use of atrazine, consistent with good plant protection practice, will not have any harmful effects on human or animal health or any unacceptable effects on the environment.” A very similar product to atrazine, called terbuthylazine, is used in EU today. No country has ever discontinued atrazine use for health or environmental safety reasons, including the European Union, and is used in more than 80 countries worldwide. Image File history File links Atrazine_use_map_1997. ... Image File history File links Atrazine_use_map_1997. ...

Atrazine is one of the most widely used pesticides in the United States with 76 million pounds of it applied each year.^[8]

Atrazine has been shown in some experiments by UC Berkeley biologist Tyronne Hayes to be a teratogen, and, even at concentrations as low as 0.1 part per billion, to emasculate male frogs by causing their gonads to produce eggs – effectively turning males into hermaphrodites.^[9] The EPA and its independent Scientific Advisory Panel (SAP) examined all available studies on this topic - including Hayes' work - and concluded there is "currently insufficient data" to determine if atrazine may affect amphibian development. Hayes, formerly part of the SAP panel, resigned in 2000 to continue studies independently.^[10] // Teratogenesis is a medical term from the Greek, literally meaning monster-birth, which derives from teratology, the study of the frequency, causation, and development of congenital malformations—misleadingly called birth defects. ... The 1st-century BC sculpture The Reclining Hermaphrodite, in the Museo Nazionale Romano, Palazzo Massimo Alle Terme in Rome A hermaphrodite is an organism that possesses both male and female sex organs during its life. ... EPA redirects here. ...

In 2003, the EPA classified the herbicide as "not likely" to cause cancer in humans, stating it did "not find any results among the available studies that would lead us to conclude that a potential cancer risk is likely from exposure to atrazine."^[11] After a 10-year science review, EPA recommended atrazine's re-registration in October 2003.^[12] Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ...

EPA considered the re-registration final when it issued the cumulative risk assessments in 2006 on the traizine herbicides, of which atrazine is one, and concluded that the herbicides pose "no harm that would result to the general U.S. population, infants, children or other...consumers."^[13]

Synonyms

2-chloro-4-(2-propylamino)-6-ethylamino-s-triazine, 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine,2-chloro-4-ethylamino-6-isopropylamino-s-triazine, 2-Chloro-4-(isopropylamino)-6-ethylamino-s-triazine, Ortho St. Augustine Weed and Feed, 6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine, A 361, aatrex, AAtrex 4L, AAtrex 80W, aatrex nine-o, actinite pk, akticon, aktikon, aktikon pk, aktinit a, aktinit pk, argezin, atazinax, Atranex, atrasine, atrataf, Atratol, atratol a, Atrazine, Atrazine 4L, Atrazine 80W, Atrazine, Atrazines, ATRAZINE (PRIMATOL), Atred, Atrex, Attrex, ATZ, Azinotox 500, Candex, cekuzina-t, chromozin, Crisamina, crisatrina, crisazine, Crisazina, Cyazine, Extrazine II, farmco atrazine, fenamine, Fenatrol, Fogard, g 30027, geigy 30,027, gesaprim, gesaprim 50, gesaprim 500, gesoprim, Griffex, Griffex 4L, hungazin, hungazin pk, inakor, Laddock, maizina, Mebazine, oleogesaprim, oleogesaprim 200, pitezin, primatol, Primatol A, primaze, radizine, Radazine, Scotts Bonus Type S, strazine, triazine a 1294, Vectal, Vectal SC, Vectral SC, Weedex, weedex a, Wonuk, zeaphos, zeapos, zeazin.

References

[http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=17520059&dopt=AbstractPlus&holding=f1000%2Cf1000m%2Cisrctnuvirlib Year 2003 (MMIII) was a common year starting on Wednesday of the Gregorian calendar. ... is the 170th day of the year (171st in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... April 27 is the 117th day of the year (118th in leap years) in the Gregorian calendar, with 248 days remaining. ... Year 2003 (MMIII) was a common year starting on Wednesday of the Gregorian calendar. ... is the 286th day of the year (287th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... April 27 is the 117th day of the year (118th in leap years) in the Gregorian calendar, with 248 days remaining. ... Year 2003 (MMIII) was a common year starting on Wednesday of the Gregorian calendar. ... is the 32nd day of the year in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era. ... April 27 is the 117th day of the year (118th in leap years) in the Gregorian calendar, with 248 days remaining. ...

 Environ Health Perspect. 2007 May;115(5):720-7. Epub 2007 Feb 5. Links 

Atrazine-induced aromatase expression is SF-1 dependent: implications for endocrine disruption in wildlife and reproductive cancers in humans.

Fan W, Yanase T, Morinaga H, Gondo S, Okabe T, Nomura M, Komatsu T, Morohashi K, Hayes TB, Takayanagi R, Nawata H. Department of Medicine and Bioregulatory Science, Graduate School of Medical Science, Kyushu University, Fukuoka, Japan. BACKGROUND: Atrazine is a potent endocrine disruptor that increases aromatase expression in some human cancer cell lines. The mechanism involves the inhibition of phosphodiesterase and subsequent elevation of cAMP. METHODS: We compared steroidogenic factor 1 (SF-1) expression in atrazine responsive and non-responsive cell lines and transfected SF-1 into nonresponsive cell lines to assess SF-1's role in atrazine-induced aromatase. We used a luciferase reporter driven by the SF-1-dependent aromatase promoter (ArPII) to examine activation of this promoter by atrazine and the related simazine. We mutated the SF-1 binding site to confirm the role of SF-1. We also examined effects of 55 other chemicals. Finally, we examined the ability of atrazine and simazine to bind to SF-1 and enhance SF-1 binding to ArPII. RESULTS: Atrazine-responsive adrenal carcinoma cells (H295R) expressed 54 times more SF-1 than nonresponsive ovarian granulosa KGN cells. Exogenous SF-1 conveyed atrazine-responsiveness to otherwise nonresponsive KGN and NIH/3T3 cells. Atrazine induced binding of SF-1 to chromatin and mutation of the SF-1 binding site in ArPII eliminated SF-1 binding and atrazine-responsiveness in H295R cells. Out of 55 chemicals examined, only atrazine, simazine, and benzopyrene induced luciferase via ArPII. Atrazine bound directly to SF-1, showing that atrazine is a ligand for this "orphan" receptor. CONCLUSION: The current findings are consistent with atrazine's endocrine-disrupting effects in fish, amphibians, and reptiles; the induction of mammary and prostate cancer in laboratory rodents; and correlations between atrazine and similar reproductive cancers in humans. This study highlights the importance of atrazine as a risk factor in endocrine disruption in wildlife and reproductive cancers in laboratory rodents and humans. ]==External links==